Tony Leighton is a Canadian writer happily retired and attempting to help others feel the same.

Freedom, One Small Brave Step at a Time

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"For someone gaga about the freedom, this struggle seems strange."

A reader wrote that line in an email to me this past week. He was referring to someone he knows who is struggling to find his way in the early days of retirement, yet enthralled with the freedom. Gaga, as my friend so strikingly put it.

On reflection, I don't see his friend's conundrum as strange at all. I think it's a natural state of confusion that follows the leaving of a career for the unknown territory of free ranging in the open world.

It’s sunnily optimistic to extol the glories of being able to do whatever you want with your time, as I often do. And yet, for some people, it's difficult not to ruminate on the losses, changes, and unknowns.

Fear rules us with a tighter grip than optimism will ever muster.

We tend to ride the What-If/What-Now/WTF! roller coaster.

My experience is that it’s a temporary condition. The ups and downs eventually smooth out. The ride becomes more like a scenic train than something that lurches your gut. I had gut lurches for about two years. My gut today is becalmed.

A useful tool for countering the What-If/What-Now/WTF! roller coaster is the True/False/Don’t Know Query.

As soon as you speculate fearfully, trigger the query: Is it true? Is it false? Or do I not actually know?

"Will my lack of [insert] cause me to [insert], which will result in devastating [insert], because it's well known that [insert] destroys [insert], especially in men?"

Not knowing is the usual honest answer.

And if that is the answer, then the fear is just a thought, an invention of the imagination, a soap bubble of the furtive mind. Certainly not real.

The prudent thinker, at that point, will puncture the fearful thought and take the next small brave step forward, into freedom, which is surely one of the most enviable states.


What's your retirement personality? (There are six.)

Need an identity anchor? Go home.